CA2739033C - Fiber or foil from polymers with high tg and process for their manufacture - Google Patents
Fiber or foil from polymers with high tg and process for their manufacture Download PDFInfo
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- CA2739033C CA2739033C CA2739033A CA2739033A CA2739033C CA 2739033 C CA2739033 C CA 2739033C CA 2739033 A CA2739033 A CA 2739033A CA 2739033 A CA2739033 A CA 2739033A CA 2739033 C CA2739033 C CA 2739033C
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- Prior art keywords
- polymer
- fiber
- poly
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- 229920000642 polymer Polymers 0.000 title claims abstract description 160
- 239000000835 fiber Substances 0.000 title claims abstract description 129
- 238000000034 method Methods 0.000 title claims abstract description 62
- 239000011888 foil Substances 0.000 title claims abstract description 50
- 230000008569 process Effects 0.000 title claims abstract description 41
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 25
- 229920000110 poly(aryl ether sulfone) Polymers 0.000 claims abstract description 39
- 238000005345 coagulation Methods 0.000 claims abstract description 26
- 230000015271 coagulation Effects 0.000 claims abstract description 26
- 239000003960 organic solvent Substances 0.000 claims abstract description 25
- 239000007788 liquid Substances 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims description 34
- 229910001868 water Inorganic materials 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 10
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 9
- 150000005846 sugar alcohols Polymers 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000011800 void material Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 46
- 229920006260 polyaryletherketone Polymers 0.000 abstract description 36
- 239000002904 solvent Substances 0.000 abstract description 25
- 239000004642 Polyimide Substances 0.000 abstract description 18
- 229920001721 polyimide Polymers 0.000 abstract description 18
- 239000000243 solution Substances 0.000 description 59
- 239000002253 acid Substances 0.000 description 25
- 125000004432 carbon atom Chemical group C* 0.000 description 22
- 229920006393 polyether sulfone Polymers 0.000 description 20
- 238000009987 spinning Methods 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- -1 poly(aryl sulfone) Polymers 0.000 description 16
- 229920002492 poly(sulfone) Polymers 0.000 description 14
- 238000006116 polymerization reaction Methods 0.000 description 14
- 229920001519 homopolymer Polymers 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- 229920001601 polyetherimide Polymers 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- 230000000875 corresponding effect Effects 0.000 description 12
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 125000005462 imide group Chemical group 0.000 description 10
- 239000004695 Polyether sulfone Substances 0.000 description 9
- ZCILODAAHLISPY-UHFFFAOYSA-N biphenyl ether Natural products C1=C(CC=C)C(O)=CC(OC=2C(=CC(CC=C)=CC=2)O)=C1 ZCILODAAHLISPY-UHFFFAOYSA-N 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 239000000178 monomer Substances 0.000 description 9
- 150000003457 sulfones Chemical class 0.000 description 9
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 238000006068 polycondensation reaction Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 229920000491 Polyphenylsulfone Polymers 0.000 description 7
- 230000001112 coagulating effect Effects 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 150000003949 imides Chemical group 0.000 description 7
- 239000003880 polar aprotic solvent Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003368 amide group Chemical group 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 239000012510 hollow fiber Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000004696 Poly ether ether ketone Substances 0.000 description 5
- 239000004962 Polyamide-imide Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- 125000001033 ether group Chemical group 0.000 description 5
- 238000001125 extrusion Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229920002312 polyamide-imide Polymers 0.000 description 5
- 229920002530 polyetherether ketone Polymers 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 239000004697 Polyetherimide Substances 0.000 description 3
- 229920003295 Radel® Polymers 0.000 description 3
- 229920004695 VICTREX™ PEEK Polymers 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000006159 dianhydride group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000635 electron micrograph Methods 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 238000001000 micrograph Methods 0.000 description 3
- 210000003739 neck Anatomy 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229920013730 reactive polymer Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 125000001174 sulfone group Chemical group 0.000 description 3
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- MYRMVFDVAQKSBC-UHFFFAOYSA-N 2,3-diphenoxybenzoic acid Chemical compound C=1C=CC=CC=1OC=1C(C(=O)O)=CC=CC=1OC1=CC=CC=C1 MYRMVFDVAQKSBC-UHFFFAOYSA-N 0.000 description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- JUPQTSLXMOCDHR-UHFFFAOYSA-N benzene-1,4-diol;bis(4-fluorophenyl)methanone Chemical compound OC1=CC=C(O)C=C1.C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 JUPQTSLXMOCDHR-UHFFFAOYSA-N 0.000 description 2
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 2
- 229940106691 bisphenol a Drugs 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000000701 coagulant Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000010327 methods by industry Methods 0.000 description 2
- 238000000386 microscopy Methods 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
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- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
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- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
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- RUETVLNXAGWCDS-UHFFFAOYSA-N (4-chlorophenyl)-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(Cl)C=C1 RUETVLNXAGWCDS-UHFFFAOYSA-N 0.000 description 1
- UPINQHZTZBBANL-UHFFFAOYSA-N (4-fluorophenyl)-(2-hydroxyphenyl)methanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=C(F)C=C1 UPINQHZTZBBANL-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 1
- PLVUIVUKKJTSDM-UHFFFAOYSA-N 1-fluoro-4-(4-fluorophenyl)sulfonylbenzene Chemical compound C1=CC(F)=CC=C1S(=O)(=O)C1=CC=C(F)C=C1 PLVUIVUKKJTSDM-UHFFFAOYSA-N 0.000 description 1
- SSUBAQORPAUJGD-UHFFFAOYSA-N 1-methylpyrrolidin-2-one;pyrrolidin-2-one Chemical compound O=C1CCCN1.CN1CCCC1=O SSUBAQORPAUJGD-UHFFFAOYSA-N 0.000 description 1
- ZDULHUHNYHJYKA-UHFFFAOYSA-N 2-propan-2-ylsulfonylpropane Chemical compound CC(C)S(=O)(=O)C(C)C ZDULHUHNYHJYKA-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
- OKISUZLXOYGIFP-UHFFFAOYSA-N 4,4'-dichlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 OKISUZLXOYGIFP-UHFFFAOYSA-N 0.000 description 1
- LSQARZALBDFYQZ-UHFFFAOYSA-N 4,4'-difluorobenzophenone Chemical compound C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 LSQARZALBDFYQZ-UHFFFAOYSA-N 0.000 description 1
- ZYEDGEXYGKWJPB-UHFFFAOYSA-N 4-[2-(4-aminophenyl)propan-2-yl]aniline Chemical compound C=1C=C(N)C=CC=1C(C)(C)C1=CC=C(N)C=C1 ZYEDGEXYGKWJPB-UHFFFAOYSA-N 0.000 description 1
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- 239000004150 EU approved colour Substances 0.000 description 1
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
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- 125000001118 alkylidene group Chemical group 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
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- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
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- AIXMJTYHQHQJLU-UHFFFAOYSA-N chembl210858 Chemical compound O1C(CC(=O)OC)CC(C=2C=CC(O)=CC=2)=N1 AIXMJTYHQHQJLU-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
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- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
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- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000007380 fibre production Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000011020 pilot scale process Methods 0.000 description 1
- 229920013655 poly(bisphenol-A sulfone) Polymers 0.000 description 1
- 229920005649 polyetherethersulfone Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920005594 polymer fiber Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- AJENTGJUWPNAEZ-UHFFFAOYSA-N propane-1,2-diol;propan-2-ol Chemical compound CC(C)O.CC(O)CO AJENTGJUWPNAEZ-UHFFFAOYSA-N 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- NJMOHBDCGXJLNJ-UHFFFAOYSA-N trimellitic anhydride chloride Chemical compound ClC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 NJMOHBDCGXJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01D5/00—Formation of filaments, threads, or the like
- D01D5/06—Wet spinning methods
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/66—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyethers
- D01F6/665—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyethers from polyetherketones, e.g. PEEK
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/74—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polycondensates of cyclic compounds, e.g. polyimides, polybenzimidazoles
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/76—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from other polycondensation products
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Mechanical Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Artificial Filaments (AREA)
- Spinning Methods And Devices For Manufacturing Artificial Fibers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10617708P | 2008-10-17 | 2008-10-17 | |
| US61/106,177 | 2008-10-17 | ||
| PCT/EP2009/063572 WO2010043705A1 (en) | 2008-10-17 | 2009-10-16 | Fiber or foil from polymers with high tg and process for their manufacture |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2739033A1 CA2739033A1 (en) | 2010-04-22 |
| CA2739033C true CA2739033C (en) | 2017-06-20 |
Family
ID=41351501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2739033A Expired - Fee Related CA2739033C (en) | 2008-10-17 | 2009-10-16 | Fiber or foil from polymers with high tg and process for their manufacture |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8637583B2 (enExample) |
| EP (1) | EP2358929B1 (enExample) |
| JP (1) | JP5624045B2 (enExample) |
| CN (1) | CN102187023B (enExample) |
| BR (1) | BRPI0919681A2 (enExample) |
| CA (1) | CA2739033C (enExample) |
| WO (1) | WO2010043705A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150322210A1 (en) * | 2012-12-17 | 2015-11-12 | Solvay Specialty Polymers Usa, Llc | Polyaryl Ether Polymers End-Capped with Phenolic Amino Acids |
| EP2956576B1 (en) * | 2013-02-13 | 2020-07-08 | President and Fellows of Harvard College | Immersed rotary jet spinning devices (irjs) and uses thereof |
| WO2014130275A2 (en) | 2013-02-22 | 2014-08-28 | Ticona Llc | High performance polymer composition with improved flow properties |
| US9534086B2 (en) | 2014-05-07 | 2017-01-03 | International Business Machines Corporation | Methods of forming poly(aryl ether sulfone)s and articles therefrom |
| CN106574184A (zh) | 2014-08-21 | 2017-04-19 | 提克纳有限责任公司 | 包含聚芳基醚酮和低环烷液晶聚合物的组合物 |
| EP3183321A1 (en) | 2014-08-21 | 2017-06-28 | Ticona LLC | Polyaryletherketone composition |
| RU2617652C1 (ru) * | 2015-12-24 | 2017-04-25 | Открытое акционерное общество "Институт пластмасс имени Г.С. Петрова" | Способ коагуляционного выделения полисульфона |
| RU2756466C2 (ru) * | 2016-11-08 | 2021-09-30 | Тейджин Арамид Б.В. | Процесс для производства волокна из полиэфиркетонкетона |
| CN117604663A (zh) | 2019-01-14 | 2024-02-27 | 哈佛学院院长等 | 聚焦旋转喷射纺丝装置及其使用方法 |
| KR102411507B1 (ko) * | 2020-08-13 | 2022-06-21 | 한국화학연구원 | 비결정성 슈퍼 엔지니어링 플라스틱 섬유 및 이의 제조방법 |
| KR20230122578A (ko) * | 2020-12-23 | 2023-08-22 | 사이텍 인더스트리스 인코포레이티드 | 제어된 형태를 갖는 폴리아크릴로니트릴계 섬유의 제조 방법 |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA847963A (en) | 1970-07-28 | Zutty Nathan | Process for preparing polyarylene polyethers | |
| CA1017097A (en) | 1962-11-06 | 1977-09-06 | Imperial Chemical Industries Limited | Manufacture of polysulphones |
| DE1545106C3 (de) | 1963-07-16 | 1979-05-31 | Union Carbide Corp., New York, N.Y. (V.St.A.) | Verfahren zur Herstellung von linearen Polyarylenpolyäthern |
| US4175175A (en) | 1963-07-16 | 1979-11-20 | Union Carbide Corporation | Polyarylene polyethers |
| NL6604887A (enExample) | 1966-04-13 | 1967-07-25 | ||
| US3634355A (en) | 1968-03-21 | 1972-01-11 | Ici Ltd | Aromatic polymers from dihalogenoben-zenoid compounds and alkali metal hydroxide |
| GB1586972A (en) | 1977-02-01 | 1981-03-25 | Ici Ltd | Production of aromatic polyethers |
| JPS5812932B2 (ja) * | 1977-06-30 | 1983-03-10 | 日本ゼオン株式会社 | 中空繊維の製造方法 |
| JPS588504A (ja) * | 1981-07-08 | 1983-01-18 | Toyobo Co Ltd | ポリスルホン中空繊維気体分離膜 |
| JPS58132111A (ja) * | 1982-01-29 | 1983-08-06 | Asahi Chem Ind Co Ltd | ポリスルホン中空糸 |
| AT377016B (de) | 1983-03-09 | 1985-01-25 | Chemiefaser Lenzing Ag | Verfahren zur herstellung von schwer entflammbaren, hochtemperaturbestaendigen polyimidfasern |
| DD233385A1 (de) | 1984-12-28 | 1986-02-26 | Adw Ddr | Verfahren zur herstellung poroeser polymerformkoerper |
| DE3814715A1 (de) | 1988-04-30 | 1989-11-09 | Basf Ag | Aus der schmelze geformte faeden aus mindestens einem aromatischen polymeren |
| DE69033282T2 (de) * | 1989-05-23 | 1999-12-30 | Teijin Ltd., Osaka | Poly(arylen-äther-keton), verfahren zur herstellung desselben und dessen verwendung |
| JPH0755980B2 (ja) * | 1989-05-23 | 1995-06-14 | 帝人株式会社 | ポリ（アリ―レンエ―テルケトン）の製造方法 |
| JP2594396B2 (ja) * | 1989-12-22 | 1997-03-26 | 三井東圧化学株式会社 | ポリイミド成形品 |
| DE69027595T2 (de) * | 1989-12-22 | 1997-01-23 | Mitsui Toatsu Chemicals | Polyimid giessling |
| DE4009208A1 (de) | 1990-03-22 | 1991-09-26 | Basf Ag | Geformte gebilde aus aromatischen polyethersulfonen, die gegen uv-strahlung stabilisiert sind und ein verfahren zu deren herstellung |
| US5207803A (en) * | 1990-09-28 | 1993-05-04 | Springs Industries | Method for dyeing aromatic polyamide fibrous materials: n,n-diethyl(meta-toluamide) dye carrier |
| US5258149A (en) * | 1990-11-27 | 1993-11-02 | W. R. Grace & Co.-Conn. | Process of making a membrane for high efficiency removal of low density lipoprotein-cholesterol from whole blood |
| US5215554A (en) * | 1991-06-12 | 1993-06-01 | Permea, Inc. | Membranes having enhanced selectivity and method of producing such membranes |
| JP3232117B2 (ja) * | 1991-11-19 | 2001-11-26 | 鐘淵化学工業株式会社 | ポリスルホン多孔質中空糸 |
| US5367046A (en) | 1992-04-10 | 1994-11-22 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Low dielectric polyimide fibers |
| EP0908541B1 (en) | 1996-03-06 | 2005-06-01 | Mitsubishi Rayon Co., Ltd. | Fibril based fibers, method of manufacturing same, spinning nozzle used in same, and moldings obtained therefrom |
| SG67983A1 (en) | 1997-06-21 | 1999-10-19 | Univ Singapore | Highly permeable polyethersulfone hollow fiber membranes for gas separation |
| GB2355464B (en) | 2000-02-11 | 2004-08-11 | Victrex Mfg Ltd | Aromatic polyetherketones |
| GB2364319B (en) | 2000-07-06 | 2003-01-15 | Gharda Chemicals Ltd | Melt processible polyether ether ketone polymer |
| WO2003097221A1 (en) | 2002-05-17 | 2003-11-27 | Para Limited | Hollow fiber membrane having supporting material for reinforcement, preparation thereof and spinneret for preparing the same |
| ES2414864T3 (es) | 2002-06-28 | 2013-07-23 | Neokidney Holding B.V. | Método para la preparación de fibras porosas funcionales |
| EP1627941A1 (en) | 2004-08-17 | 2006-02-22 | Mosaic Systems B.V. | Functional porous multilayer fibre and its preparation |
| CN1313658C (zh) | 2005-11-15 | 2007-05-02 | 北京服装学院 | 一种聚醚砜纤维及其制备方法和应用 |
| US8881915B2 (en) * | 2006-04-26 | 2014-11-11 | Toyo Boseki Kabushiki Kaisha | Polymeric porous hollow fiber membrane |
| CN101680125B (zh) * | 2007-03-23 | 2012-12-26 | 索维高级聚合物股份有限公司 | 改进的织物 |
| CN101143304A (zh) * | 2007-07-17 | 2008-03-19 | 天津工业大学 | 一种中空纤维膜及其制备方法 |
| WO2009142433A2 (ko) * | 2008-05-19 | 2009-11-26 | 한양대학교 산학협력단 | 중공사, 중공사 형성용 도프 용액 조성물 및 이를 이용한 중공사의 제조방법 |
| WO2009142434A2 (ko) * | 2008-05-19 | 2009-11-26 | 한양대학교 산학협력단 | 중공사, 중공사 형성용 도프 용액 조성물 및 이를 이용한 중공사의 제조방법 |
-
2009
- 2009-10-16 JP JP2011531503A patent/JP5624045B2/ja not_active Expired - Fee Related
- 2009-10-16 US US13/124,078 patent/US8637583B2/en not_active Expired - Fee Related
- 2009-10-16 CA CA2739033A patent/CA2739033C/en not_active Expired - Fee Related
- 2009-10-16 BR BRPI0919681A patent/BRPI0919681A2/pt not_active IP Right Cessation
- 2009-10-16 EP EP09748064.4A patent/EP2358929B1/en not_active Not-in-force
- 2009-10-16 CN CN200980141388.4A patent/CN102187023B/zh not_active Expired - Fee Related
- 2009-10-16 WO PCT/EP2009/063572 patent/WO2010043705A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP2358929B1 (en) | 2014-04-30 |
| WO2010043705A1 (en) | 2010-04-22 |
| CN102187023A (zh) | 2011-09-14 |
| BRPI0919681A2 (pt) | 2017-10-31 |
| JP2012505973A (ja) | 2012-03-08 |
| JP5624045B2 (ja) | 2014-11-12 |
| US20110263729A1 (en) | 2011-10-27 |
| CA2739033A1 (en) | 2010-04-22 |
| CN102187023B (zh) | 2014-07-09 |
| US8637583B2 (en) | 2014-01-28 |
| EP2358929A1 (en) | 2011-08-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20140916 |
|
| MKLA | Lapsed |
Effective date: 20181016 |